Chicago is one of those cities I’ve been to dozens of time, but didn’t feel like I really knew at all until this past trip. I’d been there for conferences and road trips, but each time it was too short to get a real feel for the city. I spent two weeks in Chicago and never saw the bean.

There’s so much more to Chicago than the Loop (or whatever conference center you’re chained to). People talk about the very hip West Side, but the North Side has a ton to offer. If you’re looking for a real Chicago experience — while keeping up with your deadlines — here’s how to do it.

john hancock center. Photo by Drew Hays on Unsplash

What to do and see

Walk over to the Montrose Point Bird Sanctuary for a great view of the Chicago skyline in the distance. You can walk, bike, or cross-country ski all the way downtown along the lake.

The Museum of Contemporary Art Chicago is in the Near North Side, close to Miracle Mile. It’s a must-see.

The Loyola Museum of Art is a tiny taste of European religious art. They have great special exhibits and events. It’s free, so if you’re in the neighborhood, it’s absolutely worth stopping by.

Where to work

My preferred spot to work in the North Side is Everybody’s Coffee in Uptown. I may be partial, given my experience staying with JPUSA.

If you’re looking for some intense Instagram backgrounds, check out Osimum in Lakeview. Heritage Outpost in Sheridan Park is also made for Instagram (and tucked in a residential lobby).

If you have enough self control to work around doughnuts, Firecakes is quiet during the day and has both wifi and an exceptionally clean bathroom.

The Whole Foods at Fullerton and Sheffield, like many locations, is essentially a coffee shop/coworking space. They’re open until 10p, which is later than most coffee shops.

The Museum of Contemporary Art has a public space with wifi. It’s a nice change of pace from another coffee shop — a big, beautiful open space.

Restoration Hardware is one of those spots I wish was secret, but isn’t. They’ve got plugs, wifi, and wine, so you can really make yourself at home in their displays. It’s the much classier version of working at IKEA.

Where to eat & drink

Forget the pizza, you need to have a Chicago hot dog.

The best spot for a quick, delicious, and reasonably healthy lunch is Antique Taco. There were some serious Instagram photoshoots happening while I was there.

I have two favorite brunch spots in Chicago: Longman & Eagle in Logan Square and 3 Arts Club Cafe on the Gold Coast.

Jeni’s Splendid Ice Creams live up to the name. I had the Thai peanut and it was pretty amazing. If doughnuts are more your style, Firecakes is the way to go.

For happy hour, hit the Boiler Room for their PBJ special – pizza, beer, and Jameson. They also have subway themed bathrooms, which is a little odd, but I dig it. Just be ready to pay in cash.

The classic cocktail spot is the Green Mill. If you’re out late enough you can hit the Golden House.

For the best view, get a cocktail at The Signature Room, the bar at the top of the John Hancock Center.

Okay, it’s not in the North Side, but It’s been well over a year since I ate at El Che and I still think about it. You can skip the Girl & the Goat and live your life without regrets, but you should go to El Che.

Other places of note:

Where to stay

If you’re looking for a place that feels like a real neighborhood, but still has lots to do, check out Wrigleyville and Uptown.

If you ask your friends, they’ll tell you to stay in Wicker Park or Logan Square. It’s true: these are very trendy neighborhoods with lots to do.

If you want to be close to the Loop and all the touristy things, Old Town has a little more character while still being in the middle of everything.

walking in the snow under chicago's L. Photo by Kent Henderson on Unsplash

Practical matters

It’s easy to get from either O’Hare or or Midway airport on transit. The L goes right there, although for ORD you’ll probably want to take a bus to the blue line. It’s quick and easy, no need for a cab.

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